diff --git a/src/markdown/render.ts b/src/markdown/render.ts
index 502ab69ef..111430f3a 100644
--- a/src/markdown/render.ts
+++ b/src/markdown/render.ts
@@ -93,13 +93,8 @@ export function renderMarkdownWithMarkers(ir: MarkdownIR, options: RenderOptions
   for (let i = 0; i < points.length; i += 1) {
     const pos = points[i];
 
-    while (stack.length && stack[stack.length - 1]?.end === pos) {
-      const span = stack.pop();
-      if (!span) break;
-      const marker = styleMarkers[span.style];
-      if (marker) out += marker.close;
-    }
-
+    // Close links before styles to maintain proper nesting order
+    // (links are typically nested inside styles like bold/italic)
     const closingLinks = linkEnds.get(pos);
     if (closingLinks && closingLinks.length > 0) {
       for (const link of closingLinks) {
@@ -107,6 +102,13 @@ export function renderMarkdownWithMarkers(ir: MarkdownIR, options: RenderOptions
       }
     }
 
+    while (stack.length && stack[stack.length - 1]?.end === pos) {
+      const span = stack.pop();
+      if (!span) break;
+      const marker = styleMarkers[span.style];
+      if (marker) out += marker.close;
+    }
+
     const openingLinks = linkStarts.get(pos);
     if (openingLinks && openingLinks.length > 0) {
       for (const link of openingLinks) {
diff --git a/src/telegram/format.test.ts b/src/telegram/format.test.ts
index 831782815..105626c12 100644
--- a/src/telegram/format.test.ts
+++ b/src/telegram/format.test.ts
@@ -47,4 +47,19 @@ describe("markdownToTelegramHtml", () => {
     const res = markdownToTelegramHtml("```js\nconst x = 1;\n```");
     expect(res).toBe("<pre><code>const x = 1;\n</code></pre>");
   });
+
+  it("properly nests link tags inside bold when URL is at end of bold span", () => {
+    const res = markdownToTelegramHtml("**Check https://example.com**");
+    expect(res).toBe('<b>Check <a href="https://example.com">https://example.com</a></b>');
+  });
+
+  it("properly nests link tags inside italic", () => {
+    const res = markdownToTelegramHtml("_visit https://docs.molt.bot_");
+    expect(res).toBe('<i>visit <a href="https://docs.molt.bot">https://docs.molt.bot</a></i>');
+  });
+
+  it("renders emoji before bold correctly", () => {
+    const res = markdownToTelegramHtml("🧪 **Header text**");
+    expect(res).toBe("🧪 <b>Header text</b>");
+  });
 });